Skip to main content
Mentor Academy · Harder conversations

How do I tell a mentee something they will not want to hear?

The kindest version of a hard message is the clear one. Softened to the point of ambiguity, it simply gets missed.

Read time
4 minutes
Module
Harder conversations
Session length
30 minutes
The short answer

What good looks like.

  • Say it in the first half of the session so there is time to work through it.

  • Be specific about the gap and impersonal about the person. It is the application, the portfolio or the plan that has the problem.

  • Never leave a hard truth without a route. The message is "not yet, and here is the path", not "no".

In practice

A sequence you can follow.

  1. 01

    Ask permission once

    "Can I be direct about what I am seeing?"

  2. 02

    State it in one sentence

    No preamble, no hedging.

  3. 03

    Give the evidence

    What in the work led you there.

  4. 04

    Move to the route

    Two changes that close the gap, and how long it takes.

Common mistakes

What to avoid.

  • Burying the message in praise until it disappears

  • Delivering it in the last two minutes

  • Commenting on the person rather than the work

Extra tips

Small things that make the half hour better.

Say it in the first half

Leave time to work through it together.

Ask permission once

"Can I be direct about what I am seeing?"

Aim at the work

The application has the gap, not the person.

Always give the route

"Not yet, and here is the path" is the message.

Take this guide with you.

Download a printable version of this guide: the short answer, the steps, the extra tips, the mistakes to avoid and the questions mentors ask, to read before your next session.

Questions

The things people ask first.

What if they get upset?

Slow down, acknowledge it, and stay with them. Do not retract something true.

Next: When a mentee wants a job from you.

Be clear about what you can and cannot do, in the first five minutes.